


Time and Time Again

by Partyintheimpala (orphan_account)



Category: Supernatural
Genre: Alternate Universe - Boarding School, Alternate Universe - College/University, Anal Fingering, Anal Sex, Angst, Break Up, Businessman Dean, Depressed Castiel, First Time, Fluff, Happy Ending, High School, Homophobia, It Gets Worse Before It Gets Better, M/M, Masturbation, Minor Bela Talbot/Dean Winchester, Minor Castiel/Original Female Character, Minor Character Death, Minor Character(s), Minor Violence, References to Depression, Rich Castiel, Rich Dean, Senior year, WIP, trust me it is only to continue the storyline
Language: English
Status: In-Progress
Published: 2016-08-07
Updated: 2017-08-12
Packaged: 2018-08-07 08:02:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 8,227
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7706899
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/Partyintheimpala
Summary: <blockquote class="userstuff">
              <p>Boarding school, a place where rich adults send their spoiled rich kids. For Castiel, growing up in one was second nature, he'd never known anything different. What he wasn't used to, was the new transfer student. Tall and handsome, with a respectable family, oh, and he happens to be Castiel's new roommate.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> This fic is probably going to be pretty long. I didn't want to muddle the tags but there is lots of angst and the story will continue after they graduate from school.

 

Castiel can feel the warm sun on his face as he wakes up. It would be a perfect morning if it wasn't the day he would have to give up his room. Well, more like share, but still. He'd asked his father for a single suite for his last year of high school, but he was met with a speech about how he should experience it one last year before living alone. The problem is not only that he has to share, but that the person he will be sharing with will come from another school. Because of his academic achievements he was chosen to help transfer students transition. _You're so good with people...Don't worry about it... I'm sure it will work out..._ As much as he wanted to take these affirmations to heart, he knows it will not be as easy as pie. 

He can't help but take a last look at his room. _His_ books, on _his_ shelves, next to _his_ bed, in _his_ room. He can hear his father in his head, telling him to give it a chance. He grabs his towel and shower supplies and heads to the bathroom. He's up early, no one has run down the water yet. The warm water trickling down his back relaxes him a bit. _Just come up with some rules and boundaries and you'll be fine. Easy._ His old roommate, who was also his brother, graduated last year. Leaving him to be the last Novak at the school besides his Uncle Zachariah who works as the history professor. He exits the shower and gets dressed in his uniform. Navy slacks, white shirt, black tie, navy suit jacket, and his school pin. He combs his hair neatly to the side and adjusts his pin so it is up to snuff. He looks at himself in the mirror and tells himself "one more year".

As soon as 9 am rolls around he goes to the administrative offices. He sees a bunch of boys in deep green uniforms standing around with luggage and assumes they're the transfers. He quickly assesses them and tries to find the more nerdy one, at least then he won't have to worry about any rambunctious behavior. None of them seem particularly boisterous, that is, until one boy walks in. His shirt is untucked, tie undone, he doesn't even have his jacket on. He walks in with a younger boy who seems much more rule abiding. They all start taking loudly, and pushing eachother around playfully. There's about 10 of them, ranging from freshmen to seniors and Castiel can tell they're no good. Probably from a sports centered school from the looks of it. He doesn't realize that he's staring until the one that looks like the leader approaches him. 

"What are you staring at stiff?" He says cockily. Cas freezes and tries to look around for an excuse. 

"Me? Oh, um, nothing, I just..." Cas stutters, caught off guard.

"I'm just joking with you. I'm Dean." He says, holding out his hand.

"Castiel." Cas says as he shakes his hand.

"Your tie is crooked." Dean whispers with a smirk. Cas smiles and fixes it.

"Thanks." He says awkwardly. One of his classmates joins him and the secretary gives them room numbers and keys. They show the group around campus and to their rooms. The school was built in the late 1800's and has consistent Georgian style architecture all around campus. Castiel's family is one of the main contributors and has been attending for generations. The school year doesn't start until tomorrow so there's nothing going on. It's fairly empty other then kids that got dropped off early or even stayed through summer school. Castiel visited his brothers in Germany over the summer. 

They go through each dormitory and hand out keys to the new residents. Castiel gets more and more anxious as they go down the list. Dean's name is not being called and they are getting closer and closer to Castiel's room. It's the largest and at the very end of the hallway. He continues worrying as they get closer and closer to the end of the hallway. 

"Sam Winchester." His classmate says. Dean puts his hand on the boy's shoulder and goes into the room with him. Sam is rooming with the brother of a popular senior. If he gets in this kid's good graces he will be fine. Although Cas likes to think that he is popular because of his personality he knows that his family name has something to do with it. It's down to the last two available rooms and as Castiel assumed, Dean's name is called.

"Dean Winchester." _Brothers._  Cas thinks. Cas smiles and opens the door with his key that has an engraved N in it.

"Do I get a fancy one?" Dean jokes.

"Sorry, no." Cas says as he hands him the plain duplicate. The classmate leaves and Cas stays in the room with Dean.

"I'm assuming you're my roommate?" Dean chuckles.

"Oh. Yes. Your bed is the one over there." Cas says as he crosses his arms and leans against his bed post. He watches as Dean goes over and starts unpacking. Cas watches like a hawk as Dean takes out clothes and personal items. He notices him hide something in a shirt and put it in his drawer.

"You know I can see you staring." Dean says without even turning around.

"Sorry. I've never had a roommate before other than my brothers."

"Well, I'm Dean as you know. My brother is Sam, which you probably figured out. We are Winchesters, and if you know about my family you know my mom died years ago and my dad remarried. We're old money, like you. We deal in weapons."

"What about you?"

"I just told you."

"No. You told me about your family. What about you?" Castiel asks. Of course, he knows      the Winchesters. He never had faces to put the names to, but when John Winchester remarried it was gossiped about endlessly. It was said that he never really got over Mary and that his new wife was just to fill in the gap.

"Well. I like sports, and I look out for my own."

"That's it?"

"Listen, people don't usually ask. I have that family spiel down pat as I'm sure you do too." Dean smiles when Cas rolls his eyes. "How does it go? My name is Castiel Novak, I can crush you with all the connections my family has."

"Wow. Didn't know I was  _that_ well known."

"There's not many Castiels."

"I try not to lead with a threat. It's more like, my name is Castiel Novak, my family owns the biggest import and export company in the nation."

" _Imports and exports huh?"_  Dean says teasingly.

"Bold." Castiel says as his tone changes. It's known that the Novak family are far from the most legitimate businessmen but no one would ever question them. Especially someone like the Winchesters who rely on the Novaks for product movement. 

"Woah woah, sorry. I didn't know you were so serious." Dean says as he looks at Cas a little more nervously.

"I take my family very seriously." Castiel says stoically. He has been taught to put family first his entire life. It's no laughing matter.

"I guess so." Dean says. He looks a little intimidated, but he doesn't stop with his friendly demeanor. "Sorry if I offended you."

"I know." Castiel says. "No loud music after 7, I keep the door locked, I like to keep the room clean but housekeeping comes through at 1pm on weekdays, I don't like visitors that aren't family but if you have a _visitor_ then a sock on the door would suffice." 

"No booty calls then?" Dean jokes.

"There are 3 dances with an all girl's school each school year. I can make myself scarce." Cas says seriously, although girls are not his taste, he is in no position to let a dude he just met know that he is into men. 

"That's not at all what I was asking." Dean says as he seems to stare straight through Cas. They stare at each other for an awkward amount of time after that comment. He gets a strange feeling in his stomach and decides to dismiss it as anxiety. 

"I'm going to go and see what is for breakfast."

"I'll go check on Sam."

"I don't need to know where you are all the time." Cas says matter of factly but he quickly realized how rude he sounds. He bites his lip and leaves the room as soon as possible. There's nothing that he could say that would make that exchange better. He eats breakfast with a couple friends and sees Dean across the cafeteria.

"Is that a new transfer student?" His friend Uriel asks.

"Yes." Castiel replies.

"He's hot." Uriel says as he makes eyes at Dean.

"He's my roommate." Cas mumbles as he pokes at his eggs

"You're lucky, I'm stuck with this loser." Uriel says to his roommate Virgil.

"That's harsh." Virgil laughs. "How could you be unhappy with _that."_  


  
_"_ He mentioned my family."

"Did you go all, _my family doesn't joke around_ , on him?" Uriel says as he impersonates Castiel's stoic tone.

"I can't let my family's reputation be tainted."

"Dude it's not that serious." Virgil says.

"That's where we disagree." Castile says as he takes a bitter bite of toast.

"Let me know if you guys ever, _you know_." Virgil says as he makes various hand movements. Uriel and Castiel laugh and make fun of him. "You know what I mean!"

"Ew. No thank you." Cas says.

"What's ew about _that?"_ Uriel says as he blatantly gestures to Dean. Cas kicks him under the table.

"I have to room with him for the next year. Plus I don't have time for that."

"Oh, that's right. Castiel is still pure as a daisy." Virgil says mockingly.

"I don't think I like your tone." Castiel jokes. He knows they're just joking but his virginity is definitely not the topic he wants to be on. His longest relationship lasted two months and fizzled out when the school year ended. He isn't set on saving himself for marriage or anything, but having his first time be with someone special would be nice. He catches himself thinking about Dean and forces himself to stop. _He is your roommate, you don't even know him._ He tells himself. It's going to be a long year. 


	2. Chapter 2

The first day of school was _always_ hectic; with the new students it is even more of a mess. Castiel navigates through the sea of parents and children. He tries to get outside where it isn't so damn busy. He takes a deep breath once he reaches the outdoors and relishes the September sun beating down on his face. The school is far enough into the country that air is crisp and clean. One thing he has always loved about the school was its location. Surrounded by trees and wildlife, it has always been a serene hiding place. He walks into the forest, following the path he was shown many years ago by his brothers. He is able to walk blind if he had to. After walking for about ten minutes the path leads to an opening in the trees. There's a stream in the middle, surrounded by grass and large rocks. Cas takes off his shoes and walks into the soft green grass with a book in hand. He makes his way to a rock on the bank and discards his jacket on the ground.

Cas sits on the rock and sets down his book as he rolls up his pants. He dips his feet in the cool water and opens his book to where he folded the corner. Where he last left off, there was great tragedy between the main characters. They are deeply in love, but they are forbidden to see each other because of their parent's disapproval. Even though it's cliché, Cas loves to read young adult romance novels. The only downside is that he has to choose all the stories with straight couples. Anything else might get him found out. He knows somewhere inside him he yearns for what these characters have. The reckless abandon, the lack of foresight, no responsibilities, _and the love._ But he does not envy their pain or their sadness without the other. He flips page after page, unbothered by the setting sun. He continues to read, blissfully unaware. After hours of reading a firefly lands on his leg and his relaxation turns to panic. He shuts his book and swears at himself for losing track of time. He gets his uniform back in order and races to the school, hoping they haven't started dinner yet. He gets to the cafeteria and realizes exactly _how_ late he is. With his book in hand he walks in as tall and proud as possible. You could hear a pin drop as everyone turned to look at him. He soon realizes that the principal, Mr. Weston, was in the middle of his beginning of the year speech.

"Nice of you to join us Mr.Novak." He says sternly, Cas knows his uncle absolutely seething behind the principal.

"I apologize. It won't happen again." He says before he takes his seat with the other seniors. From what he can tell, the speech is about hard work and perseverance. It's also about welcoming the new students and transfers. He drones on about these things, repeating himself and drawing out the speech for way too long. Castiel is seated away from his friends because of his tardiness. He stares at his salad, waiting for the principal to finish his speech. He hasn't eaten much of anything the entire day. Staring turns to longing and all he is thinking is about how the salad will taste. His classmate, nudging him, pulls him out of his daydream. Cas looks up to see Mr.Weston standing right in front of him.

"Castiel Novak! Please explain to your peers how the transfer student program works." He says. Castiel stands and begins to explain everything. He tells himself to stop daydreaming. It's getting him in trouble he could easily avoid. Castiel gives his speech about the transfer students like a well-rehearsed script. The principal then explains to treat them like any other student and to help them find their way around. Dinner seems to take forever. By the time the principal finishes his speech you can hear everyone's stomach growling. Everyone digs in and devours their salads. They completely abandon their table manners and wait eagerly for the main course. Castiel knows he can't slip up again so he eats his salad slowly, in time with the teachers. It's hard not to shovel the leafy greens into his mouth and call it a night, but he has to keep up his reputation. He can feel his uncle watching him; Castiel knows how it reflects on the family when he messes up.

He notices his uncle staring angrily; he's definitely going to get a call from his parents. His uncle Zachariah was never fond of any of his nieces or nephews. He never liked kids, and even though most of them were adults now, he still didn't like them. The only person he is even remotely nice to is Castiel's father. Castiel's father has always tried to remain in all their lives. Whenever you talked to him it was like listening to a parenting how-to book with a flare for family values. He only knew how to attempt to give life lessons or how to talk business. Sometimes if he was drunk he would tell you stories about his time at school or how he met Castiel's mother. Still, Castiel loved his father, and enjoyed his company. Well, more like holidays. Christmas and Easter (the most important holidays according to him).

The main course is pork tenderloin with asparagus and mashed potatoes. Castiel takes his time, making a point to his uncle. By the time dinner is over it is well into the night. Everyone is dismissed and heads back to their rooms. Castiel begins to walk to his room when someone taps his shoulder.

"This place is huge! How do you know where to go? I almost got lost on the way here." Dean says as he walks with Cas.

"You'll get used to it." Castiel says as he keeps walking.

"Until then I guess you'll have to walk me to class." Dean jokes, nudging Cas playfully.

"I guess so." Cas says, not really wanting to talk.

"Hey where were you today? I tried to find you but it was hard in the crowds."

"I guess we were in different places, I was helping with new students all day." Cas lies.

"Why were you late?" Dean asks.

"I had things to do."

"What book are you reading?" Dean asks.

"You ask _a lot_ of questions." Cas says, putting the book further under his arm.

"Sorry, sometimes I forget that people don't always want to talk to me."

"Uh huh."

"I hear so much about you, I wanted to get to know you. But if you're busy avoiding me that's fine." Dean jokes.

"I had a tiring day and I'm a little worn out." _You want to get to know me? What have people been saying?_

_"_ Ok. Sorry." Dean says. Dean stays right behind Castiel the way back to the room. They weave between people and manage to get all the way down the hallway with little problems. Once they are inside their room Cas starts undressing like usual. He tosses each article of clothing to a pile on the floor and doesn't realize the blank stare from Dean until he's in his boxers.

"Are you ok?" Castiel asks. He's grown up in boarding schools, seeing your roommate is no rarity.

"I'm fine." Dean says with a fake smile. Cas ignores it and puts his dirty clothes in the clothes hamper. He can feel Dean's eyes on him as he walks around the room getting ready for bed. If anything, it gives him confidence. Despite his unassuming appearance and presence he is very sure of himself. Confidence is important, plus if people think you're weak you can easily prove them wrong. Castiel is no weight lifter but he'd be lying if he said he was out of shape. He relishes the attention and smiles to himself that it's from Dean Winchester.

"Why are you staring at me?" Castiel asks as he sits on his bed. Dean immediately looks away and stutters as he opens his dresser.

"I'm not, what do you mean?" Dean says with obvious nervousness as he turns around and shuffles around in his drawer.

"Ok then." Cas says, giddy that Dean is nervous. He doesn't know why he wants to intimidate this boy but he does.

\---

A couple weeks pass, everyone gets used to their schedules. Castiel and Dean barely talk, and when Dean tries Cas admits he shuts it down. It's not that he dislikes Dean. The problem is that he doesn't think they have anything in common. School is boring as usual, it's like everything is in slow motion during class. Each tick of the clock is like torture in the nearly silent English class. He tries counting along with the seconds to pass the time, knowing it will only draw it out longer. What's worse is that his next class is History. Not only is his jerk uncle the teacher, but also Dean sits right next to him. Dean doesn’t bother him, but they can't seem to have a normal conversation. It always ends in strange looks or a long silence. Their roommate situation is fine despite their odd chemistry.

"Castiel." His teacher says. Cas reluctantly tears his eyes away from the clock and looks at his teacher.

"Yes?" He says, knowing she saw him daydreaming.

"They want you at the office. I expect your work to be turned in by the end of the day."

"Ok." _You don't have to tell me twice._ He gathers his things and heads over to the front desk. He hopes it’s his father, telling him he can test out of school and start working. He knows it's not. His father almost never visits the school. The office is empty apart from the receptionist, when he walks in the rapid clicking stops.

"You can go in." She says before returning to typing. He nods and goes into the office, sitting there is the principal. He is a rather intimidating man, not particularly large or muscular, but the way he looks at you is enough. He has known Castiel his entire life, but Castiel can't recall a time that he wasn't referred to as _Mr.Weston._ He has a large beard that seems to be groomed rather meticulously. His office always smells good, probably due to his affinity to candles. He has never been mean, but Cas has also never seen him laugh. He takes a seat and waits for Mr.Weston to finish writing what looks like a letter of recommendation.

"Castiel, you are the head of the transfer student program this year, yes?" He asks as he puts the paper into a folder and sets to the side.

"Yes sir." Castiel says.

"How has it been going? Do they seem comfortable?" Mr.Weston asks.

"Um, I guess so. I don't really know a lot of them because they're in lower grades."

"What about your room mate? Winchester."

"He's ah, he's fine, but we don't hang out. Or even talk." Cas says. There's no point in lying.

"Why?” Mr.Weston asks quizzically.

"Busy I guess, I don't really know." Cas says, knowing he could have said something more professional.

"If you're going to be an ambassador for our school, you can't only be popular with your classmates. You have to make and impression on everyone who goes to this educational institution. Understood?" Mr.Weston says.

"I don't know if I do." Cas admits.

"You and Winchester need to lead by example. I've heard that the transfers are keeping to themselves. We need to blend everyone together."

"You want me to force a friendship with my room mate?" Cas asks, knowing if he doesn't succeed he will get a stern letter from his parents about hard work.

"In short, yes. Who knows, you might have more in common then you think."

"I'll try." He says, thinking about how hard it will be to befriend someone he can hardly have small talk with.

"Ok Castiel, you're dismissed." He stands and holds out his hand which Castiel shakes firmly as his father taught him. He leaves the office and gets a hall pass for his next class. The last thing he needs is shit from his uncle about being punctual. He makes his way back to class but takes the long way, hoping to waste as much time before actually making it to class. As he drags his feet he is well aware that a hall monitor could catch him, but he'd risk a lot to miss his uncle's class. The long corridors feel endless as he passes dorm after dorm. He has lived in C dorm his entire high school experience. It was built on the original school grounds that are not attached to any of the main buildings. He's always liked that. There is more privacy and a lack of supervision.

"Castiel Novak!" He hears the angry yell of his uncle beckoning him to class and has let go of the peace he had earlier. He can see his uncle leaning out of the classroom and waving his arm telling him to hurry. "Do you have a pass?" He asks. Castiel fishes it out of his pocket and hands it to him, he almost looks disappointed that he can't scold his nephew. "Take a seat and catch up." He says as Castiel makes his way to the back of the classroom. He takes a seat and copies the notes of the person next to him. Class goes by pretty fast. As the school day winds down Cas gets more and more nervous about befriending Dean. The most they talk is when Cas explains directions around the school.

As soon as the bell rings Castiel goes to his room and changes into regular clothes, more relatable right? He doesn't know why he is so nervous. He is a people person, he's charming, he's charismatic, or so he thought. Once he is dressed he goes to his friend's room. He walks in to be greeted by Uriel who is still in his uniform.

"Where's Virgil?" Cas asks.

"Not back from class yet. Has he told you about Franklin?"

"He’s with a sophomore? No way." Castiel exclaims.

"No no, turns out he's his half brother. Big scandal. His dad has been covering it up for years." Uriel says as he puts away his books.

"Wow. So I'm guessing he doesn't want to talk about it."

"Definitely not. Would you want to talk about that?" Uriel says with a laugh.

"No, that's a long cover up though." Cas says. Things like this come out sometimes. Affairs are unfortunately pretty common.

"That's what I was thinking! You mind if I change?"

"You know I don't care." Cas says as he takes a seat at Virgil's desk.

"So what's been happening with you?" Uriel asks as he starts to change into a button up shirt and slacks.

"Well, Mr.Weston wants me to be best friends with Dean." Cas says.

"Winchester?"

"Yep." Cas nods and crosses his arms.

"What's the problem with that? He follows you around like a puppy." Uriel jokes.

"He did until I was kind of a dick to him."

"What did you do?"

"I was never really nice in the first place, I think he just gave up." Cas says, knowing he could have been much more accommodating.

"All you have to do is be nice to him and I'm sure he'll want to get to know you again." Uriel pulls on his pants and tucks in his shirt. Most people dress the way Uriel does. Some people wear jeans the first couple weekends. They end up assimilating to the weird second uniform the school seems to have.

"What do I say? Sorry for being a jerk, our principal wants us to be friends." Cas asks.

"He doesn't need to know that. Try it out, see where things go."

"You're acting like I'm interested in him."

"Go get him tiger." Uriel teases. Cas says goodbye and goes to his room to read. He waits for Dean long into dinner hours. At around 7 he decides to give up on waiting and goes to get some food before it's over. When he walks in he spots Dean immediately. He's sitting at a long table that is filled with people, transfers and home students alike. They are all listening to him intently as he tells some grand story. Sam is sitting right next to him, he looks like he has heard the story hundreds of times but he smiles anyway. Cas can't hear what Dean is saying but there are waves of laughter as he grabs a plate of food. He turns to see all the students leaving the dining hall, leaving Dean and Sam at the table still. He takes a seat across from them and starts to eat.

"Hey Castiel." Dean says a little awkwardly. "I think your friends are over there." He looks very confused that Cas would sit with him.

"Were you about to leave?" Cas asks.

"Yeah kind of." Dean says, "Do you need something?"

"No, I wanted to talk."

"About what?"

"Um, how was your day?" Cas asks, trying desperately to make small talk. Dean chuckles and finishes what is left in his cup.

"My day was fine. I finally figured out how to work the shower." Dean says unenthusiastically.

"Oh cool! They can be a little tricky." Cas says with a fake positivity anyone would notice.

"Listen, I don't know who put you up to talking to me, but it's pretty clear that you don't want to actually get to know me. I'll see you around." Dean says before leaving the dining hall with Sam following right behind him. Cas sits at the table alone and picks at his food. Rarely does he get rejected in such a way. Rarely does he fail so spectacularly at talking to someone. Rarely does he want so badly to prove someone wrong. He knows it's what he deserves for ignoring him so much, but now it's like a challenge. He scarfs down his food and heads to his room. He needs this challenge. He goes back to their room and finds Dean studying at his desk.

"Hey, Dean." Castiel says timidly.

"Yes?" Dean answers, not even looking over, his eyes trained on his books.

"I was thinking we should get to know each other more. We are roommates after all."

"What a surprise." Dean remarks, standing up and facing Castiel. Cas stares at him right in the eyes and tells his brain to stop focusing on how gorgeous his roommate is. "I'm guessing Mr.Weston talked to you about uniting all the students and for us to be role models. Your plan to befriend me to kiss the principal's ass is pathetic. I'd prefer to befriend people who actually want to get to know me, not some fake brat who is trying to do as they're told."

Castiel feels like he's being read like a book. His ogling ends and turns to embarrassment. He does _not_ like being called out, who does? But being challenged like this is something completely foreign. He squints and decides to be honest. "You did catch me with the whole kiss ass thing." Castiel admits, refusing to break eye contact. "But I'd appreciate it if you left out the name calling, I'm not usually such a dick to people."

"You're stuck up and pretentious. I tried to be nice and I tried to get to know you only to be shot down." Dean

"I have been an ass to you. I figured you were a sports playing, huge ego, jock."

"What would give you that impression?"

"Have you seen yourself?" Cas says, as he looks Dean up and down.

"You'll have to make it up to me for being so rude." Dean says, sitting back down and rolling a pencil eraser between his teeth.

"Make it up to you?" Castiel questions. He sits down on his bed and crosses his arms.

"Yes." Dean says smugly.

"I'm not just going to-" Castiel starts. He hopes he isn't going to be roped into some stupid dare or public humiliation.

"Actually try to get to know me. Not for Mr.Weston." Dean interrupts. "If you're not an asshole as you say, then prove it."

"What does that even mean?" Castiel says in protest.

"What does it mean to get to know someone? Come on Castiel, I thought you were brighter then that."

"Fine, why are you here? Why did you and your brother transfer here, they usually only transfer rejects." Castiel asks just to get the ball rolling.

"My step mom is kind of hard to deal with." Dean replies with honesty.

" _Hard to deal with?_ "

"She acts like Sam and I are inconveniences to her." Before Castiel can inquire more, Dean announces, "My turn." He leans back in his chair and points the pencil at Cas. "What kind of books do you read? You never tell me."

"I like young adult novels the kind with cliché romance and an action-y plot." Castiel confesses. Dean raises his eyebrows as if to tease but instead he simply says, “Your turn."

"Why did you want to befriend me in the first place?" Castiel asks plainly.

"You were honest and acted like a real person. Sure you seemed a little stiff, but I figured it was because we were strangers." Dean says.

"Stiff?" Castiel says with fake outrage.

"Hey it's my turn, what do you want to do when you're older?"

"Honest answer?" Castiel asks.

"No, I want you to lie." Dean teases.

"A writer. Novelist maybe. I know I will probably never be one, but, I can always dream." Castiel admits.

"Why not?"

"Being in business is what's expected of me."

"Do _you_ want to be a businessman?" Dean asks.

"No, but I always knew I would have to do it." Castiel says.

"Who says?"

"No one directly, but my father would prefer if-" Cas starts.

"This is your life, not your dad's." Dean interrupts.

"Fine, what do you want to do?" Castiel changes the focus instead of becoming serious and protective.

"I want to take over my father's business."

"You _want_ to?" Castiel says in disbelief. Almost everyone _has_ to go into their respective famil _y_ business _._ It is rare that they want to.

"I always have." Dean says.

"Have a girlfriend?" Castiel says it lie word vomit. I was supposed to stay a thought in his head.

"No, no girlfriend, you?" Dean says, he blushes and looks at the ground.

"I'm sadly single." Castiel says with a smile.

"So no boyfriend either." Dean says with a hesitant look.

"Don't believe every rumor you hear." Castiel says seriously, attempting to deflect. His sexuality is often questioned on campus. He prefers to keep it to himself and his close friends. "I'm going to study for a while and then go to bed." Castiel says, put Dean directness.

"Talk to you tomorrow then." Dean says quietly.

"Yeah, tomorrow." Cas says, he gets his books out and studies like he said he would. Dean fiddles around on his phone for a while until he goes to bed. Castiel hopes this gets easier. If they are really going to be friends they have to do more then interrogate each other.

**Notes for the Chapter:**

> Hope you liked it! I have up until chapter 4 nearly finished. I'll try to post fairly often but I don't have a very good track record if I'm being honest.


	3. Chapter 3

**Notes for the Chapter:**

> Hello! Smut is up ahead. I don't know why I feel like I need to put a disclaimer but here it is.

Castiel knew it was risky, but it had been weeks. Before Dean, he would just wait for his brother to be at some various club or event, they knew how to stay out of each other’s hair. But Dean. Dean doesn't know the meaning of privacy. They practically have the same schedule and Cas can't get a minute alone. He tries to act as normal as possible as he makes his way back to his room during study hall. He can feel the palms of his hands clam up in anticipation. He can't unlock the door fast enough. Once inside he carefully takes off his pants and loosens his tie before locking the door and lying in bed. His cock is already twitching in delight. He has been neglecting himself that's for sure. He caresses his hipbones and closes his eyes. He tries to imagine someone and ends up vaguely remembering porn he watched before. His breath catches and he continues teasing himself. With his eyes closed the feeling of his arousal is much more satisfying. He licks his lips and let's out a little gasp as he runs his hand over his growing erection. 

He relishes each tiny touch and stroke he gives himself, he knows it will be over way too soon if he starts too quickly. He starts with his cock in his fist as he strokes himself slowly. He thinks of the porn, two younger men were sucking each other off. He thinks of how it would feel as he drags his thumb over the slit. He thinks of how another man's hand would feel on his aching length. He thinks of how good it would feel to fuck someone. He lets out a small moan and bucks into his fist eagerly. He twists his wrist carefully and can't contain the slew of profanity that escapes his mouth. He slows himself down and strokes slowly, wanting to drag this out. He lets go and rolls to the side of his bed. He grabs the lube (which he has for wishful thinking and occasions like these) from the bedside table. He spreads the lube on his fingers and goes back to stroking. With his eyes closed he slowly reaches down and starts to press against his rim. The feeling is nothing new, but it still feels good. As he presses further he feels the slight burn of the intrusion. Despite the pain he continues to press in, his head falls back as he tries to get to that sweet spot. He squirts more lube into his finger and starts to thrust it in and out until he is comfortable enough to add another. "Fuck..." He whispers, as he knows he's getting close. The head of his cock leaks pre-cum as he gets closer to climax. He thinks of one of the men blowing him again and he starts to gasp. He gets closer and closer as he thrusts up into his hand. 

He doesn't realize at first when his imagination changes the man's hair to a light brown. He thinks nothing of it when the man has freckles. Suddenly he realizes who his fantasy is. Before he can comprehend what is happening he hears the latch of the door close. He opens his eyes and sees his roommate right in front of him. He comes so hard and can't stop making eye contact with Dean. It's unlike any other orgasm he has ever had. It rips through him and leaves him panting on his bed. 

"Oh! I'm sorry, I thought..." Dean says as he turns away and looks at the wall. Cas scrambles to get a pillow to cover himself. He can't believe that just happened. He literally had his fingers in his ass and he was jacking off.

"No. It's my fault. Sorry. I didn't think you would be back." Cas says quickly, hoping Dean will just leave. He feels high, as embarrassing as it is, it felt fucking good to have Dean watch him. His face must be bright red.

"I forgot a book. Are you um, decent?" Dean says as he keeps his hand over his eyes.

"Yeah." Cas says as he clutches the pillow to his crotch. Cas watches as Dean grabs a book from his desk and can't help but notice his bulge. His large bulge. 

"I'll just, go, we can forget this happened." Dean says, trying to leave as fast as possible.

"Sounds good. Um. Sorry."

"Yeah." Dean says uncomfortably. Cas can see how aroused Dean is. If he were bold he would do something, but instead he just looks away and waits for him to leave. The ecstasy wears off and he feels like an absolute mess. The come on his stomach is just embarrassing. _Why is Dean aroused? Why did I think of him? Is he my type? Does he really like dudes? Do I have a chance with him?_ A million questions race through Castiel's brain. Mainly confusion. He gets out of bed and wipes himself off with a towel from his shower earlier. He knows there's no way this won't bite him in the ass. He just had to go for fingering today. What macho super straight dude does that in their free time? 

He puts on his clothes and decides to go to the shower. He can at least clear his thoughts there. He gets undressed and gets into one of the stalls. The water runs lukewarm from the earlier showers. He settles and takes what he can get. _Should I tell my friends? No they might make a scene of it. What about Dean? Should we talk about what happened or just leave it? We agreed to forget about it but the whole interaction left more questions than answers. Why did I imagine Dean? Out of all people why Dean? He's attractive but not that attractive. Who am I kidding? He's gorgeous. Why would I turn him on? Why am I thinking about his dick?_ Cas can feel himself getting more and more turned on just by what happened. His traitor of a dick won't just let him process what happened. He strokes lazily and keeps any noise to a minimum; he is in the public showers after all. Determined to get this over quickly he strokes faster and leans against the wall.

He freezes when he hears someone enter and go to a shower stall down the row. He waits for the water to start running before attempting to finish himself off. He goes back to stroking and tries not to think of Dean. He fails miserably and ends up fantasizing again. Just the thought of Dean's arousal makes Cas whimper quietly. If he could get his hands on it, or his mouth. He exhales sharply, his cock aching for release. He grinds into his hand and sighs in relief when he comes. Cleanup is quick and he hopes his dick will behave while he finishes out his shower. He gets out and puts his clothes back on, hoping his absence to study hall was not noticed. He checks the time to see that he only has 10 minutes before his next class. On his way out of the showers he recognizes the clothes outside of the shower stall, Dean. After he sees that he practically runs out. He doesn't want to deal with that again. 

He gets to his World History class early and takes a seat in the back. You'd think having your uncle as the teacher would be a good thing, but in reality it was the worst. He was expected to know everything and if he didn't he was punished more harshly then other students. He opens his textbook and bites on the eraser side of his pencil while he waits. It doesn't even take a minute before Zachariah is criticizing him. "Cut that out, that is no way to present yourself, and your tie is crooked."

"No one is even in here, calm down." Cas replies, fixing his tie as best he can without a mirror.

"I'm still your teacher Castiel, I won't take your disrespect."

"Sorry, Professor." He says smarmily. Enough has happened today, he doesn't need his Uncle jumping down his throat. Zachariah leaves and Castiel goes back to thinking about what happened. Or what is going to happen once they inevitably have to sleep in the same room. Dean is his friend. His hot, sexy, funny, nice, green eyed, freckled, friend who also might be into dudes. If anything he probably ruined any chance of anything. He doesn't even know if he will be able to look Dean in the eyes. The other problem is how often they are together. Not only does the principal expect them to be best buddies, Cas actually enjoys his company. So completely ignoring Dean is off the list of possibilities. He could confront him about his obvious boner, but that could go very wrong if Cas just accuses him like that. Maybe forgetting it even happened would be the way to go about it.

Luckily he doesn't have to see Dean until dinner. Even then, Dean probably doesn't want to see him either. He sighs and starts to jot down the objectives of the day. He ponders these thoughts throughout the rest of the class. By the end of what seemed like forever, he decides he needs to tell someone. He sees Uriel in the hallway and quickly joins him. "I need to talk to you and Virgil."

"About what?"

"Nothing. Just, I need to talk to you two in private."

"Has something happened?" Virgil says as he joins them in walking to their dorm.

"You could say that, come on." Castiel says as they shuffle into Uriel and Virgil's room. "So, um, I was, taking care of myself, and-"

"Castiel be blunt." Uriel says.

"I was masturbating in my room during study hall." Castiel spits out.

"Uh huh." Virgil says, suddenly interested in where this is going.

"Complete with lube and fingers."

"Yeah."

"And Dean walked in on me. I was above covers, and he saw everything." Cas says.

"What did he do?" Uriel asks curiously.

"This is why I'm confused, he was aroused I think." Cas says quietly.

"You think?" Virgil says.

"He had quite a noticeable bulge."

"Castiel this is huge! You have to ask him out."

"What if he isn't gay?" Cas worries.

"He got an erection from watching you jack off, that sounds gay in my book." Virgil adds.

"Listen, I don't want to get beat up, or to be outed. That's not an option for me." Castiel knows it would be bad if any of this got out.

"He probably assumes you're gay already, or a very progressive straight guy." Uriel says as he tries to be comforting.

"I'm hoping for the latter."

"Cas we know you like him." Virgil says.

"He is a good friend."

"A friend you obviously want to bang." Uriel laughs.

"I don't want that."

"Castiel Novak, I have never seen you look at someone like you look at him. In the 6 years I've known you. Even your ex, it doesn't compare." Uriel says. Cas doesn’t want to think about his ex,

"He is my roommate, I don't want to ruin what we had going."

"It might be a little late."

"Just ask him. If he's a real friend he won't get upset." Virgil suggests.

"Fine. You might be right. Wish me luck." Cas says, he leaves and heads straight back to his room. He hopes he has some time to process alone but that is not a luxury he receives. As soon as he walks in, Dean is sitting at his desk.

"I know we said we weren't going to talk about it, but I need to get something off my chest." Dean says as he folds his hands in his lap.

"I do too, but you have to promise not to get offended or tell anyone."

"Same for me." Dean says. He looks pale as a ghost.

"I can go first if you want." Castiel offers.

"No, I can go, um, earlier I'm sure you noticed that I was kind of, staring at you."

"Staring at me? I think anyone would stare."

"That's not what I'm saying. Um, I've enjoyed getting to know you, and I just, I wanted to ask you out. With me. On, um, a date." Dean stutters as he looks at the ground nervously.

"A date?" Cas responds in shock.

"Yes."

"You're, I mean, are you gay?"

"Yes, and, I hope I'm not jumping to conclusions in assuming you are too." Dean says.

"What gave it away? My friend group or what you witnessed earlier."

"Lets say a bit of both."

"That's fair." Castile says, still recovering from being so surprised.

"So what do you say about that date?"

"Yes, I'd enjoy that." Castiel agrees.

"Tomorrow? 6?"

"Sounds good." Cas says, he doesn't know what to do. It's like when you say goodbye to someone and then walk out into the parking lot with them. He smiles awkwardly and then sits on his bed with one of his books. They stay silent for a while until Dean pipes up. 

"If you ever have to jack off you can just tell me to leave you alone." Dean says.

"Noted. Sorry about that, by the way."

"It's fine." Dean replies.

"Where are we going tomorrow?"

"I don't actually know, I didn't think you'd say yes."

"Why not?"

"I didn't know if you were gay for one, you're also Castiel Novak, I had no clue if you even went on dates." Dean jokes.

"How long have you known that you liked boys? If you don't mind me asking." Castiel wonders.

"Since I knew it was an option, I think I was probably 11 or 12. You?"

"Um, it started as a disinterest in girls. With my older brothers making such a big deal about dating and sex, I quickly realized I wasn't sexually attracted to women." Castiel explains.

"I've never been in a long term relationship with anyone."

"I went a couple months last year with a senior, we broke it off over the summer." Cas says, not wanting Uriel or Virgil to bring it up.

"I've never found anyone I wanted to date. We can still be like, friends right?"

"Yeah, at least I hope so."

"I'm going to try and finish this paper." Dean says as he turns back to his desk.

"Ok, I'm heading to dinner then."

"Ok."

"Okay..." Castiel says awkwardly, not knowing where to go with this. He ends up just leaving and going to dinner. He finds Uriel and Virgil and sits with them. 

"You've been gone 20 minutes, what happened?" Virgil asks.

"We're going on a date, um tomorrow." Castiel says. It’s weird to even say aloud.

"You are?" Uriel says, knowing not to mention Dean's name.

"Yes." Cas replies.

"Where?" Virgil asks.

"I'm not sure, I think he is choosing."

"Lets hope this goes better than your other relationship." Virgil says.

"This is not a relationship, this is a date."

"Whatever you say." Uriel goes back to eating and smirks at Castiel.

"What?" Castiel says after taking a sip of water.

"I can't believe you snagged the hottest one here." Uriel chuckles. Castiel elbows him playfully and laughs.


End file.
